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[ bleep ] >> five minutes trying to do it the right way! i'm going to show you what i'm made of! >> but gilbert proved to be more than just a violent man. he also showed us a thoughtful, creative side. in the last interview we did with gilbert, he seemed resigned to his fate of spending the rest of his life most likely alone in a small cell. >> at this point, you just look back and realize that the best part of it's over with anyway. >> but five years later, we would discover that gilbert's appearances on "lockup" had opened up a new chapter in his life. she goes by the name of angel, preferri...

First became involved with gilbert shortly after seeing him on "lockup." angel had initially contacted another holman inmate featured on the series, sherman moore, who held the job of prison barber. it was moore who acted as match-maker. >> wrote to sherman and developed a friendship with sherman. >> it's like you pulled a flattop fade out of your head? >> is that what you want? >> yeah. >> but i also saw the segment on bobby and i inquired about bobby, you know, what kind of a person is he? >> i was telling them all about me drinking that bottle of scope up in west jefferson. >> sherman encou...

Something to hustle, unlike the rest of these people out there. >> gilbert told us he is looking forward to the wedding but must be released from ad seg before the couple can be granted permission to be married. and even though angel has resigned to the fact that gilbert will never leave prison, that doesn't stop her from imagining a more idyllic home life. >> i daydream about simple things, what it would be like just to make bobby a breakfast plate and bring it to him or tell him, get it yourself, i ain't your maid. i love everything about him. i love his temperament, i love his personality, ...

It just happens. >> and after four months of calls and letters, angel decided to make the 700-mile trip from illinois to alabama, and she visited bobby for the first time. >> it was only three hours, and it was very special. he was sitting next to me, and i could see bobby out of the corner of my eye just grinning and staring at me. it was really cute. >> over the next few months, angel made the trip two more times, and on her third visit, gilbert had something special planned. >> bobby took my hand and he said, "i have nothing for you but this. i can't financially support you. all i can do is...

Something to hustle, unlike the rest of these people out there. >> gilbert told us he is looking forward to the wedding but must be released from ad seg before the couple can be granted permission to be married. and even though angel has resigned to the fact that gilbert will never leave prison, that doesn't stop her from imagining a more idyllic home life. >> i daydream about simple things, what it would be like just to make bobby a breakfast plate and bring it to him or tell him, get it yourself, i ain't your maid. i love everything about him. i love his temperament, i love his personality, ...